Sulfamide derivatives and cosmetic use thereof

ABSTRACT

The present invention relates to the cosmetic use of a compound of formula (I) 
                         
and also the cosmetically acceptable salts thereof, solvates thereof and isomers thereof, for non-therapeutic skincare. The invention also relates to compounds of general formula (II)

This is a Division of application Ser. No. 11/289,551 filed Nov. 30,2005. The disclosure of the prior application is hereby incorporated byreference herein in its entirety.

BACKGROUND

This non provisional application claims the benefit of FrenchApplication No. 04 52821 filed on Nov. 30, 2004 and U.S. ProvisionalApplication No. 60/638,371 filed on Dec. 27, 2004.

The present invention relates to a method for manufacturing a cosmeticcomposition comprising the use of sulfamides and derivatives thereof inthe field of skincare and for example as a skin moisturizer, to novelsulfamide derivatives and to cosmetic compositions containing them.

The stratum corneum, which forms the interface with the dehydratingexternal environment, serves for example to delay the excessive loss ofwater originating from the deeper layers of the epidermis. The stratumcorneum also protects against mechanical attack and the passage ofchemical products and foreign microorganisms. It also constitutes thefirst line of defence against UV radiation.

The stratum corneum, which is 10 μm thick, is composed of verticallystacked corneocytes surrounded with a matrix of lipid-enrichedmembranes. Thus, it is a two-compartment system that may be comparedwith a brick wall, composed of anuclear cells (the “bricks”) and ofintercellular lamellar membranes (the “cement”).

Urea is one of the ingredients widely used in moisturizing formulations.However, it can greatly modify the skin barrier by increasing thetransepidermal water loss (TWL), which significantly reduces the barrierfunction of the stratum corneum.

Glycerol, another reference active agent in this field, has the drawbackof making formulations tacky when it is used at high concentration.

There is thus a need to find alternative solutions in the field of skinmoisturization.

The inventors have discovered that certain sulfamide derivatives ofgeneral formula (I) described below may be good moisturizers and mayhave a beneficial effect in terms of elasticity on the stratum corneum.

Thus, in one exemplary embodiment, the present invention relates to amethod for manufacturing a cosmetic composition comprising the use ofcompounds of general formula (I):

in which

R¹, R², R³ and R⁴ represent, independently of each other:

a hydrogen atom,

a (C₁-C₁₀)alkyl group, for example a (C₁-C₆)alkyl group and for examplea (C₁-C₄)alkyl group, optionally substituted with 1 to 5 groups chosenfrom —OR⁵, —NR⁶R⁷ and —SiR⁸R⁹R¹⁰, in which optionally 1 to 3 carbonatoms of the said (C₁-C₁₀)alkyl group may be replaced, independently ofeach other, with a hetero atom chosen from a nitrogen atom, a sulfuratom, an oxygen atom, a silicon atom and a sulfonyl group (—SO₂—)including, for example, the group —O—SO₂—NR⁶R⁷, or alternatively

(R¹ and R²) and/or (R³ and R⁴) may form, with the nitrogen that bearsthem, a 5- to 7-membered heterocycle optionally substituted with 1 to 4hydroxyl groups and/or a group —NR⁶R⁷, the heterocycle being chosen forexample from pyrrolidine, piperazine, morpholine, azepane, pyrazolidine,imidazolidine and oxazolidine, and also partially unsaturated homologuesthereof, for example pyrrole, pyridine or pyrimidine derivatives, oralternatively

(R¹ and R³) or (R² and R⁴) may form, with the group —N—(SO₂)—N— thatbears them, a 5- to 9-membered heterocycle optionally substituted with 1to 4 hydroxyl groups and/or a group NR⁶R⁷ and chosen for example from1,2,5-thiadiazolidine, 1,2,6-thiadiazinane, 1,2,7-thiadiazepane,1,2,8-thiadiazocane and 1,2,9-thiadiazonane 1,1-dioxides,

R⁵, R⁶ and R⁷ represent, independently of each other,

a hydrogen atom, or

a (C₁-C₆)alkyl group, and

R⁵ may also represent a group such that —OR⁵ represents a phosphate orsulfate group,

R⁸, R⁹ and R¹⁰ represent, independently of each other, a (C₁-C₆)alkylgroup,

and also the cosmetically acceptable salts thereof, solvates thereofsuch as hydrates, and isomers thereof, for non-therapeutic skincare, andfor example as moisturizers, for example at a non-alkaline pH.

In another exemplary embodiment, the present invention relates to acosmetic composition comprising a compound of formula (I), in aphysiologically acceptable medium, for example at a non-alkaline pH.

In another exemplary embodiment, the present invention relates to acosmetic composition comprising a compound of formula (I) as describedabove, with the exclusion of N,N′-bis(2-hydroxyethyl)sulfamide, in aphysiologically acceptable medium, for example at a non-alkaline pH.

In another exemplary embodiment, the present invention relates to acosmetic composition comprising, in a physiologically acceptable medium,for example at a non-alkaline pH, a compound of formula (I) as describedabove also comprising at least one additive chosen from an oil, a fattysubstance, a gelling agent, a filler, a UV-screening agent, an odourabsorber and a dyestuff.

In another exemplary embodiment, the present invention relates to acosmetic treatment process for non-therapeutic skincare and/or formaking up the skin, characterized in that it comprises the applicationto the skin of at least one cosmetic composition according to thepresent invention comprising a compound of formula (I) as defined above.

The Compounds of General Formula (I)

In the context of the present invention, an exemplary embodiment is themethod for manufacturing a cosmetic composition comprising the use ofthe compounds of general formula (I) in which

R¹, R², R³ and R⁴ represent, independently of each other:

a hydrogen atom,

a (2,2-dimethyldioxolane)methyl group,

a (C₁-C₁₀)alkyl group optionally substituted with 1 to 5 groups chosenfrom —OR⁵, —NR⁶R⁷ and —SiR⁸R⁹R¹⁰, or alternatively

(R¹ and R³) or (R² and R⁴) form, together with the —N—(SO₂)—N— groupthat bears them, a 6- to 8-membered heterocycle chosen from1,2,6-thiadiazinane, 1,2,7-thiadiazepane and 1,2,8-thiadiazonane1,1-dioxides, optionally substituted with 1 to 3 hydroxyl groups,

R⁵ represents

a hydrogen atom,

a (C₁-C₄)alkyl group,

a group —SO₂NRR′, or

a group —SiR⁸R⁹R¹⁰,

R⁶ and R⁷ represent, independently of each other:

a hydrogen atom, or

a (C₁-C₄)alkyl group,

R⁸, R⁹ and R¹⁰ represent, independently of each other, a (C₁-C₄)alkylgroup, and

R and R′ represent, independently of each other, a hydrogen atom or a(C₁-C₄) alkyl group,

and also the cosmetically acceptable salts thereof, solvates thereofsuch as hydrates and isomers thereof, for non-therapeutic skincare, andfor example as moisturizers, for example at a non-alkaline pH.

These compounds of formula (I) will be referred to hereinbelow as“compounds A”, for reasons of simplicity.

Another exemplary embodiment is the method for manufacturing a cosmeticcomposition comprising the use of the compounds of general formula (I)in which

R¹, R², R³ and R⁴ represent, independently of each other:

a hydrogen atom,

a (C₁-C₆)alkyl group optionally substituted with 1 to 5 hydroxyl groups,1 or 2 —SiMe₃ groups or with a group —O—SO₂NRR′, or alternatively

(R¹ and R³) represent a hydrogen atom and (R² and R⁴) together form,with the —N—(SO₂)—N— group that bears them, a 1,2,7-thiadiazepane1,1-dioxide group optionally substituted with 1 or 2 hydroxyl groups ora 1,2,6-thiadiazinane 1,1-dioxide group optionally substituted with 1 or2 hydroxyl groups,

R and R′ represent, independently of each other:

a hydrogen atom, or

a (C₁-C₄)alkyl group,

and also the cosmetically acceptable salts thereof, solvates thereofsuch as hydrates, and isomers thereof, for non-therapeutic skincare, andfor example as moisturizers, for example at a non-alkaline pH.

These compounds of formula (I) will be referred to hereinbelow as“compounds B”, for reasons of simplicity.

In the context of the present invention, the term “alkyl” means a linearor branched, saturated or unsaturated, cyclic or non-cyclichydrocarbon-based chain. Among the alkyl groups that are suitable foruse in the invention, mention may be made for example of the methyl,ethyl, isopropyl, n-propyl, n-butyl, t-butyl, —CH₂-t-butyl, pentyl,n-hexyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclohexylmethyl, heptyl,octyl, nonyl, decyl, norbornyl and adamantyl groups.

Among the (C₁-C₁₀)alkyl groups in which 1 to 3 carbon atoms may bereplaced with a hetero atom, mention may be made of the(2,2-dimethyldioxolane)methyl group.

In the context of the present invention, the term “non-alkaline pH”means a pH of between 4 and 7 and for example between 5 and 6.

Some of the compounds of formula (I) are known. The following documentsdescribe some of them and give useful indications regarding the modes ofsynthesis described below.

-   L. F. Audrieth, M. Sveda, H. Sisler, M. Josetta Butler, Chemical    Review, 1940, 26, 49-94,-   Paquin, Angewante Chemie, 1948, 60, 11/12, 316-320,-   K. Sprott, P. Hanson, Journal of Organic Chemistry, 2000, 65,    7913-7918,-   M. McReynolds, K. Sprott, P. Hanson, Organic Letters, 2002, 4, 26,    4673-4676,-   H. Preuschhof, H-U. Heyne, Organic Syntheses, Collective volume 6,    78, step 1,-   J. M. Dougherty, D. A. Probst, R. E. Robinson, J. D. Moore, T. A.    Klein, K. A. Snelgrove, P. R. Hanson, Tetrahedron, 2000, 56,    9781-9790,-   G. Dewynter, M. Abdaoui, L. Toupet, J-L. Montero, Tetrahedron    Letters, 1997, 38, 8691-8694, and-   Y. Masui, H. Watanabe, T. Masui, Tetrahedron Letters, 2004, 45,    1853-1856, G. M. Atkins, E. M. Burgess, Journal of the American    Chemical Society, 1968, 90, 4744-4745.    Compounds According to the Invention and Mode of Preparation    Thereof.

The compounds of formulae (II), (III) and (N) defined below also formpart of the invention.

According to one exemplary embodiment, the invention is related tocompounds of formula (II)

in which:

R¹² represents a hydrogen atom, a group —SiR⁸R⁹R¹⁰, a (C₁-C₉)alkyl groupoptionally substituted with 1 to 5 groups chosen from —OR⁵, —NR⁶R⁷ and—SiR⁸R⁹R¹⁰, in which optionally 1 to 3 carbon atoms of the said(C₁-C₉)alkyl group may be replaced, independently of each other, with ahetero atom chosen from a nitrogen atom, a sulfur atom, an oxygen atomand a silicon atom or a sulfonyl group (—SO₂—),

R¹¹ represents a hydrogen atom, a (C₁-C₆)alkyl group optionallysubstituted with 1 to 5 groups chosen from —OR⁵ and/or —SiR⁸R⁹R¹⁰ oroptionally with a group —OSO₂—NRR′,

R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R and R′ being as defined above for thecompounds A and the compounds B of formula (I), and also the solvatesthereof such as hydrates, salts thereof and isomers thereof.

In one exemplary embodiment, the compounds of formula (II) are those inwhich:

R¹² represents a hydrogen atom, an —SiMe₃ group or a (C₁-C₆)alkyl groupoptionally substituted with 1 to 5 hydroxyl groups, 1 or 2 —SiMe₃ groupsor with an —O—SO₂NH₂ group,

R¹¹ represents a hydrogen atom or a (C₁-C₆)alkyl group optionallysubstituted with 1 or 2 groups chosen from —OR⁵ and —SiMe₃,

R⁵, R⁸, R⁹ and R¹⁰ being as defined above for the compounds A and thecompounds B of formula (I), and also the solvates thereof such as thehydrates, salts thereof and isomers thereof.

In one exemplary embodiment, the compounds of formula (II) are those inwhich:

R¹² represents a hydrogen atom, an —SiMe₃ group or a (C₁-C₆)alkyl groupoptionally substituted with a hydroxyl group,

R¹¹ represents a hydrogen atom or a (C₁-C₆)alkyl group optionallysubstituted with 1 or 2 hydroxyl groups, and

R⁸, R⁹ and R¹⁰ each represent a methyl group, and also solvates thereofsuch as hydrates, salts thereof and isomers thereof.

According to another exemplary embodiment, the invention relates to thecompounds of formula (III)

in which:

R¹³ represents a (C₁-C₉)alkyl substituted with 1 to 5 groups chosen from—OR⁵ and —NR⁶R⁷, or a group —O—SO₂NRR′,

R^(13′) represents a hydrogen atom or a (C₁-C₄)alkyl group, and

R⁵, R⁶ and R⁷ are as defined above for the compounds A and the compoundsB of formula (I),

R and R′ being as defined above for the compounds A and the compounds Bof formula (I),

and also solvates thereof such as hydrates, salts thereof and isomersthereof.

In one exemplary embodiment, the invention relates to the compounds offormula (II) in which R¹³ represents a (C₁-C₉)alkyl substituted with 1to 5 groups chosen from —OR⁵ and a group —O—SO₂NRR′, R⁵ representing ahydrogen atom, a (C₂-C₄)alkyl a group —SO₂NRR′, or a group —SiR⁸R⁹R¹⁰with R⁸, R⁹, R¹⁰, R and R′ being as defined above for the compounds Aand the compounds B of formula (I).

In one exemplary embodiment, the compounds of formula (III) are those inwhich:

R¹³ represents a (C₁-C₉)alkyl group substituted with 1 to 5 hydroxylgroup(s) or with an —O—SO₂NH₂ group, and

R^(13′) represents a hydrogen atom or a methyl group, and also solvatesthereof such as hydrates, salts thereof and isomers thereof.

According to yet another exemplary embodiment, the invention relates tothe compounds of formula (IV)

in which:

X and X′ take, independently of each other, the meaning of R⁵ as definedabove for the compounds of formula (I) and Y and Y′ represent,independently of each other, a hydrogen atom, a group —CH₂Z, in which Zrepresents an amine group or a group —NR⁶R⁷ or —OR⁵, or alternatively

at least one of the groups

forms, independently of each other, a dimethyldioxolane group, oralternatively:

X and X′ are hydrogen atoms and Y and Y′ together form a covalent bond,

R¹, R³, R⁵, R⁶ and R⁷ take the same meaning as that defined for thecompounds of formula (I), and X, X′, Y and Y′ advantageously do notsimultaneously represent a hydrogen atom.

A subject of the invention is, for example, the compounds of formula(IV) in which Y and Y′ are not simultaneously a hydrogen atom when X andX′ simultaneously represent a —CH₃ group.

According to one exemplary embodiment, the compounds of formula (IV) arethose in which:

X and X′ are hydrogen atoms and Y and Y′ represent a group

—CH₂OR⁵, or alternatively

at least one of the groups

forms a dimethyldioxolane group, or alternatively

X and X′ are hydrogen atoms and Y and Y′ together form a covalent bond,and

R¹, R³ and R⁵ take the same meaning as that defined by the compounds offormula (I).

In one exemplary embodiment, the compounds of formula (IV) are those inwhich:

X and X′ are hydrogen atoms and Y and Y′ represent a —CH₂OH group, oralternatively

X and X′ are hydrogen atoms and Y and Y′ together form a covalent bond,and

R¹ and R³ represent a hydrogen atom or a (C₁-C₆)alkyl group.

The salts that are acceptable for the non-therapeutic use of thecompounds described in the present invention include the conventionalnon-toxic salts of the said compounds, such as those formed from organicor mineral acids. Examples that may be mentioned include the salts ofmineral acids, such as sulfuric acid, hydrochloric acid, hydrobromicacid, hydriodic acid, phosphoric acid or boric acid. Mention may also bemade of the salts of organic acids, which may comprise one or morecarboxylic, sulfonic or phosphonic acid groups. They may be linear,branched or cyclic aliphatic acids or alternatively aromatic acids.These acids may also comprise one or more hetero atoms chosen from O andN, for example in the form of hydroxyl groups. Mention may be made forexample of propionic acid, acetic acid, terephthalic acid, citric acidand tartaric acid.

When the compound of formula (I) comprises an acid group, theneutralization of the acid group(s) may be performed with a mineralbase, such as LiOH, NaOH, KOH, Ca(OH)₂, NH₄OH, Mg(OH)₂ or Zn(OH)₂; orwith an organic base such as a primary, secondary or tertiaryalkylamine, for example triethylamine or butylamine. This primary,secondary or tertiary alkylamine may comprise one or more nitrogenand/or oxygen atoms and may thus comprise, for example, one or morealcohol functions; mention may be made especially of2-amino-2-methylpropanol, triethanolamine, 2-dimethylaminopropanol and2-amino-2-(hydroxymethyl)-1,3-propanediol. Mention may also be made oflysine or 3-(dimethylamino)propyl amine.

The solvates that are acceptable for the non-therapeutic use of thecompounds described in the present invention include conventionalsolvates such as those formed during the final step of preparation ofthe said compounds, due to the presence of solvents. Examples that maybe mentioned include the solvates due to the presence of water or oflinear or branched alcohols, for instance ethanol or isopropanol.

The compounds of formula (I) may be prepared according to techniquesthat are well known to those skilled in the art, for example accordingto a scheme 1 described below.

The standard modes for obtaining sulfamide are performed starting withsulfuryl chloride.

The amines (or diamines) chosen to give the compounds of formula (I) maybe reacted (sequentially for the dissymmetric compounds) with anelectrophilic source of SO₂, such as sulfamide H₂NSO₂NH₂, sulfurylchloride SO₂Cl₂, or sulfonylbis(2-oxazolidine) in a suitable solvent(for example, respectively, acetonitrile, pyridine or dimethylformamidefor sulfamide, or, for example, dichloromethane or tetrahydrofuran forsulfuryl chloride), for example at a temperature ranging from 0 to 140°C. in the presence or absence of a base, for instancediazabicycloundecene, triethylamine or pyridine.

The methods for synthesizing the novel compounds of formulae (II), (III)and (IV), respectively, are detailed below.

The compounds of formula (II) may be prepared according to scheme 2below:

The compounds (II) may be obtained in two ways:

either using sulfamide by reacting one mole of silyl amine of formula(VI), for example in a polar solvent such as acetonitrile,dimethylformamide or pyridine, for example at a temperature of between 0and 140° C. in the presence or absence of a catalytic amount of base,for instance diazabicycloundecene, to give the compounds of formula (V),followed by a second addition of one mole of amine R¹¹NH₂, for exampleunder similar conditions,

or using chlorosulfonyl isocyanate by performing a sequential additionof tert-butanol and of silyl amine of formula (VII), for example, in asolvent such as dichloromethane or ethyl acetate, for example between 0and 20° C. in the presence of a base, for instance triethylamine orpyridine, in order to obtain a dissymmetric sulfamide in which the NH₂group, protected in the form of tert-butoxycarbonyl, is released bymeans of an acidic treatment with, for example, hydrochloric acid ortrifluoroacetic acid; compound (II) may then be formed via addition ofone mole of amine of formula R¹¹NH₂ in a polar solvent such asacetonitrile, dimethylformamide or pyridine, for example at atemperature of between 0 and 140° C. and in the presence or absence of acatalytic amount of base, for instance diazabicycloundecene.

The compounds of formula (III) may be prepared according to scheme 3below:

Chlorosulfonyl isocyanate is sequentially reacted with one mole oftert-butanol, followed by one mole of amine of formula (IX) in thepresence of a base such as triethylamine or pyridine, for example in asolvent such as dichloromethane or ethyl acetate, for example at atemperature of between 0 and 20° C. The N-protected compound of formula(VIII) in tert-butoxycarbonyl form is then deprotected in acidic mediumwith, for example, hydrochloric acid or trifluoroacetic acid, forexample at room temperature, to give the compounds of formula (III).

The compounds of formula (IV) may be prepared according to scheme 4,which is a particular form of scheme 1:

The amines (or diamines) of respective formulae (X) and (XI) chosen togive the compounds of formula (IV) are reacted (sequentially for thedissymmetric compounds) with an electrophilic source of SO₂, such assulfamide H₂NSO₂NH₂, sulfuryl chloride SO₂Cl₂, orsulfonylbis(2-oxazolidine), in a suitable solvent (for example,respectively, acetonitrile, pyridine or dimethylformamide for sulfamide,or, for example, dichloromethane or tetrahydrofuran for sulfurylchloride), for example at a temperature ranging from 0 to 140° C. in thepresence or absence of a base, for instance diazabicycloundecene,triethylamine or pyridine.

The table below collates the compounds that may preferably be used inthe context of the present invention.

TABLE 1 No. Chemical name Formula 1 Sulfamide

2 N-(2-hydroxyethyl)sulfamide

3 N-(3-hydroxypropyl)sulfamide

4 N-(2,3-dihydroxypropyl)sulfamide

5 N-(4-hydroxybutyl)sulfamide

6 N-(2,3,4,5,6-penta- hydroxyhexyl)sulfamide

7 N-Methyl-N-(2,3,4,5,6-penta- hydroxyhexyl)sulfamide

8 N-[trimethylsilylmethyl]sulfamide

9 N-[bis(trimethylsilyl)methyl]sulfamide

10 N,N″-bis(hydroxyethyl)sulfamide

11 N,N″-bis(hydroxypropyl)sulfamide

12 N,N″-bis(hydroxybutyl)sulfamide

13 N,N″-bis (2,3-dihydroxy- propyl)sulfamide

14 N,N″-bis[(2,2-dimethyl-1,3-dioxolan- 4-yl)methyl]sulfamide

15 N-[bis(trimethylsilyl)methyl]-N″-(2- hydroxyethyl)sulfamide

16 N-[(trimethylsilyl)methyl]-N″-(2- hydroxyethyl)sulfamide

17 2-[(aminosulfonyl)amino]ethyl sulfamate

18 3-[(aminosulfonyl)amino]propyl sulfamate

19 (+/−) 1,2,7-thiadiazepane-4,5-diol 1,1- dioxide

Cosmetic Formulations

In one exemplary embodiment, the present invention relates to a cosmeticcomposition comprising a compound of formula (I) as described above,with the exclusion of N,N′-bis(2-hydroxyethyl)sulfamide, in aphysiologically acceptable medium, for example at a non-alkaline pH.

In one exemplary embodiment, the present invention relate to a cosmeticcomposition comprising, in a physiologically acceptable medium, forexample at a non-alkaline pH, a compound of formula (I) as describedabove also comprising at least one additive chosen from an oil, a fattysubstance, a gelling agent, a filler, a UV-screening agent, an odourabsorber and a dyestuff.

These cosmetic compositions in which the compounds (I), (II), (III) or(IV) may be used are useful for non-therapeutic skincare and/or formaking up the skin. They are useful for example for moisturizing theskin.

They may show their efficacy as a non-therapeutic, i.e. a preventive,skin maintenance treatment. They may also be used as a non-therapeuticskin treatment after the appearance of skin moisturization disorders.

In this second case, this appearance of skin moisturization disordersmay be for example independent of irritation caused by the placing incontact of the skin with a bleaching agent, for example a chlorinatedbleaching agent, for example based on hypochlorite.

In addition, the said cosmetic compositions may be for example not usedfor hygiene, purposes, and for example they preferably do not containany detergent.

Finally, the cosmetic compositions of the invention may be for exampleformulated under non-alkaline conditions, for example at a pH close tothat of the skin, for example at a pH of between 5 and 6.

The compounds of formula (I), (II), (III) or (IV) may be present in thecosmetic compositions in contents ranging from 0.01% to 20%, for examplefrom 0.01% to 15% and for example from 0.1% to 10% by weight relative tothe total weight of the cosmetic composition.

The compositions used according to the invention contain aphysiologically acceptable medium, i.e. a medium that is compatible withskin tissues such as the skin and the scalp. This physiologicallyacceptable medium may consist for example of water and optionally of aphysiologically acceptable organic solvent chosen, for example, fromlower alcohols containing from 1 to 8 carbon atoms and for example from1 to 6 carbon atoms, for instance ethanol, isopropanol, propanol orbutanol; polyethylene glycols containing from 6 to 80 ethylene oxideunits and polyols, for instance propylene glycol, isoprene glycol,butylene glycol, glycerol and sorbitol.

The compositions according to the invention may be in any galenical formconventionally used for topical application, and for example in the formof aqueous or aqueous-alcoholic solutions, oil-in-water (O/W) emulsions,water-in-oil (W/O) emulsions or multiple emulsions (triple: W/O/W orO/W/O), aqueous gels, or dispersions of a fatty phase in an aqueousphase by means of spherules, these spherules possibly being polymernanoparticles such as nanospheres and nanocapsules or lipid vesicles ofionic and/or nonionic type (liposomes, niosomes or oleosomes). Thesecompositions are prepared according to the usual methods.

In addition, the compositions used according to the invention may bemore or less fluid and may have the appearance of a white or colouredcream, a pomade, a milk, a lotion, a serum, a paste or a mousse. Theymay be optionally applied to the skin in aerosol form. They may also bein solid form, for example in the form of a stick.

When the composition used according to the invention comprises an oilyphase, it contains for example at least one oil. It may also containother fatty substances.

As examples of oils that may be used in the composition of theinvention, mention may be made of:

hydrocarbon-based oils of animal origin, such as perhydrosqualene;

hydrocarbon-based oils of plant origin, such as liquid triglycerides offatty acids containing from 4 to 10 carbon atoms, for instance heptanoicor octanoic acid triglycerides or alternatively, for example, sunfloweroil, corn oil, soybean oil, marrow oil, grapeseed oil, sesame seed oil,hazelnut oil, apricot oil, macadamia oil, arara oil, castor oil, avocadooil, caprylic/capric acid triglycerides, for instance those sold by thecompany Stéarineries Dubois or those sold under the names “Miglyol 810”,“812” and “818” by the company Dynamit Nobel, jojoba oil or shea butteroil;

synthetic esters and synthetic ethers, for example of fatty acids, forinstance oils of formulae R₁COOR₂ and R₁OR₂ in which R₁ represents thefatty acid residue containing from 8 to 29 carbon atoms and R₂represents a branched or unbranched hydrocarbon-based chain containingfrom 3 to 30 carbon atoms, such as, for example, purcellin oil, isononylisononanoate, isopropyl myristate, 2-ethylhexyl palmitate,2-octyl-dodecyl stearate, 2-octyldodecyl erucate or isostearylisostearate; hydroxylated esters such as isostearyl lactate, octylhydroxystearate, octyldodecyl hydroxystearate, diisostearyl malate,triisocetyl citrate and fatty alkyl heptanoates, octanoates anddecanoates; polyol esters, for instance propylene glycol dioctanoate,neopentyl glycol diheptanoate and diethylene glycol diisononanoate; andpentaerythritol esters, for instance pentaerythrityl tetraisostearate;

linear or branched hydrocarbons of mineral or synthetic origin, such asvolatile or non-volatile paraffin oils, and derivatives thereof,petroleum jelly, polydecenes, and hydrogenated polyisobutene such asParleam oil;

fatty alcohols containing from 8 to 26 carbon atoms, for instance cetylalcohol, stearyl alcohol and the mixture thereof (cetylstearyl alcohol),octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol,oleyl alcohol or linoleyl alcohol;

partially hydrocarbon-based and/or partially silicone-based fluoro oils,for instance those described in document JP-A-2 295 912;

silicone oils, for instance volatile or non-volatile polymethylsiloxanes(PDMSs) containing a linear or cyclic silicone chain, that are liquid orpasty at room temperature, for example cyclopolydimethylsiloxanes(cyclomethicones) such as cyclohexasiloxane; polydimethylsiloxanescomprising alkyl, alkoxy or phenyl groups, that are pendent or at theend of a silicone chain, these groups containing from 2 to 24 carbonatoms; phenyl silicones, for instance phenyl trimethicones, phenyldimethicones, phenyltrimethylsiloxydiphenylsiloxanes, diphenyldimethicones, diphenylmethyldiphenyl-trisiloxanes,2-phenylethyltrimethyl siloxysilicates and polymethylphenylsiloxanes;

mixtures thereof.

In the list of oils mentioned above, the expression “hydrocarbon-basedoil” means any oil mainly comprising carbon and hydrogen atoms, andoptionally ester, ether, fluoro, carboxylic acid and/or alcohol groups.

The other fatty substances that may be present in the oily phase are,for example, fatty acids containing from 8 to 30 carbon atoms, forinstance stearic acid, lauric acid, palmitic acid and oleic acid; waxes,for instance lanolin, beeswax, carnauba wax or candelilla wax, paraffinwax, lignite wax or microcrystalline waxes, ceresin or ozokerite,synthetic waxes such as polyethylene waxes, Fischer-Tropsch waxes;silicone resins such as trifluoromethyl-C1-4-alkyl dimethicone andtrifluoropropyl dimethicone; and silicone elastomers, for instance theproducts sold under the name “KSG” by the company Shin-Etsu, under thename “Trefil”, “BY29” or “EPSX” by the company Dow Corning, or under thename “Gransil” by the company Grant Industries.

These fatty substances may be chosen in a varied manner by a personskilled in the art so as to prepare a composition having the desiredproperties, for example in terms of consistency or texture.

According to one exemplary embodiment of the invention, the compositionaccording to the invention is a water-in-oil (W/O) or oil-in-water (O/W)emulsion. The proportion of the oily phase of the emulsion may rangefrom 5% to 80% by weight and for example from 5% to 50% by weightrelative to the total weight of the composition.

The emulsions may contain at least one emulsifier chosen fromamphoteric, anionic, cationic and nonionic emulsifiers, used alone or asa mixture, and optionally a co-emulsifier. The emulsifiers are chosen ina suitable manner depending on the emulsion to be obtained (W/O or O/W).The emulsifier and the co-emulsifier may be present in the compositionin a proportion that may range, for example, from 0.3% to 30% by weightand for example from 0.5% to 20% by weight relative to the total weightof the composition.

Examples of emulsifiers that may be mentioned for the W/O emulsionsinclude dimethicone copolyols such as the mixture of cyclomethicone andof dimethicone copolyol, sold under the name “DC 5225 C” by the companyDow Corning, and alkyldimethicone copolyols, such as the laurylmethiconecopolyol sold under the name “Dow Corning 5200 Formulation Aid” by thecompany Dow Corning, and the cetyldimethicone copolyol sold under thename “Abil EM 90®” by the company Goldschmidt. Surfactants for W/Oemulsions that may also be used include a crosslinked elastomeric solidorganopolysiloxane comprising at least one oxyalkylene group, such asthose obtained according to the procedure of Examples 3, 4 and 8 ofdocument U.S. Pat. No. 5,412,004 and of the examples of document U.S.Pat. No. 5,811,487, for example the product of Example 3 (synthesisexample) of U.S. Pat. No. 5,412,004, and such as the product sold underthe reference KSG 21 by the company Shin-Etsu.

Examples of emulsifiers that may be mentioned for the 0/W emulsionsinclude nonionic emulsifiers such as oxyalkylenated (more particularlypolyoxyethylenated) fatty acid esters of glycerol; oxyalkylenated fattyacid esters of sorbitan; oxyalkylenated (oxyethylenated and/oroxypropylenated) fatty acid esters; oxyalkylenated (oxyethylenatedand/or oxypropylenated) fatty alcohol ethers; sugar esters, for instancesucrose stearate; and mixtures thereof, such as the mixture of glycerylstearate and of PEG-40 stearate.

In a known manner, the cosmetic or dermatological composition of theinvention may also contain adjuvants that are common in cosmetics ordermatology, such as gelling agents, film-forming polymers, preservingagents, solvents, fragrances, fillers, UV-screening agents,bactericides, odour absorbers, dyestuffs, plant extracts and salts. Theamounts of these various adjuvants are those conventionally used in thefield under consideration, for example from 0.01% to 20% of the totalweight of the composition. Depending on their nature, these adjuvantsmay be introduced into the fatty phase and/or into the aqueous phase.

The compounds of formulae (I), (II), (III) and (IV) may be combinedtogether, or with other skin moisturizers not in accordance with formula(I) and/or with at least one other cosmetic active agent.

Additional cosmetic active agents that may for example be mentionedinclude active agents acting on the barrier function of the skin, activeagents that promote skin moisturization and desquamating agents.

The term “desquamating agent” means any compound capable of acting:

either directly on desquamation by promoting exfoliation, such asβ-hydroxy acids, in particular salicylic acid and its derivatives(including 5-n-octanoylsalicylic acid); α-hydroxy acids, such asglycolic acid, citric acid, lactic acid, tartaric acid, malic acid ormandelic acid; urea; gentisic acid; oligofucoses; cinnamic acid; extractof Saphora japonica; resveratrol;

or on the enzymes involved in the desquamation or degradation ofcorneodesmosomes, such as glycosidases, stratum corneum chymotrypticenzyme (SCCE), or even other proteases (trypsin, chymotrypsin-like).Mention may be made of agents for chelating mineral salts: EDTA;N-acyl-N,N′,N′-ethylenediaminetriacetic acid; aminosulfonic compoundsand for example (N-2-hydroxyethylpiperazine-N′-2-ethane)sulfonic acid(HEPES); 2-oxothiazolidine-4-carboxylic acid (procysteine) derivatives;α-amino acid derivatives of the type such as glycine (as described inEP-0 852 949 and sodium methylglycinediacetate sold by BASF under thetrade name “Trilon M”); honey; sugar derivatives such asO-octanoyl-6-D-maltose and N-acetylglucosamine.

Among the active agents acting on the barrier function of the skin, orthat promote skin moisturization, mention may be made of:

either a compound acting on the barrier function, in order to keep thestratum corneum moisturized, or an occlusive compound, for exampleceramides, sphingoid-based compounds, lecithins, glycosphingolipids,phospholipids, cholesterol and its derivatives, phytosterols(stigmasterol, β-sitosterol or campesterol), essential fatty acids,1,2-diacylglycerol, 4-chromanone, pentacyclic triterpenes such asursolic acid, petroleum jelly and lanolin;

or a compound that directly increases the water content of the stratumcorneum, such as threalose and its derivatives, hyaluronic acid and itsderivatives, glycerol, pentanediol, sodium pidolate, serine, xylitol,sodium lactate, polyglyceryl acrylate, ectoin and its derivatives,chitosan, oligosaccharides and polysaccharides, cyclic carbonates,N-lauroylpyrrolidonecarboxylic acid and N-α-benzoyl-L-arginine;

or a compound that activates the sebaceous glands, such as steroidderivatives (including DHEA) and vitamin D and its derivatives.

The composition may be in the form of a non-therapeutic care and/ormakeup product, and also in the form of a lip balm.

In yet one exemplary embodiment, the invention relates to a cosmetictreatment process for non-therapeutic skincare and/or for making up theskin, characterized in that it comprises the application to the skin ofat least one cosmetic composition according to the present inventioncomprising at least one compound of formula (I), (II), (III) or (IV) asdefined above or a mixture thereof in all proportions.

Among the applications of makeup type that may be envisaged by means ofthe cosmetic treatment process, mention may be made for example offoundations, makeup rouges, eyeshadows, concealer products and bodymakeup products.

In another exemplary embodiment, the invention relates to a method forpreparing a dermatological composition for moisturizing the skin and forexample for treating dryness of the skin or for treating dry skincomprising the use of a compound of formula (I), (II), (III) or (IV) asdefined above, or a mixture thereof.

The examples below illustrate the invention without, however, limitingits scope.

The elemental analyses and the NMR spectra confirm the structures of theproducts obtained.

The numbers given in parentheses in the example titles correspond tothose in Table 1 given above.

EXAMPLE 1 Synthesis of N,N″-(2,3-dihydroxypropyl)sulfamide (Compound 13)

To a solution of 1.55 ml of methamine dioxolane in 25 ml ofdichloromethane and 1.84 ml of triethylamine are added dropwise, at 0°C., 482 μl of sulfuryl chloride. After addition, the reaction mixture iswarmed slowly to 20° C. The reaction mixture is diluted withdichloromethane and washed with water and then with saturated sodiumchloride solution. The organic phase is dried over sodium sulfate andthen concentrated under reduced pressure to give 1.6 g of a white solididentified as N,N″-bis[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]sulfamide.

This compound,N,N″-bis[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]sulfamide, is thensuspended in water in the presence of Dowex® 50WX8 acidic resin sold byAldrich. The reaction medium dissolves rapidly and the reaction progressis monitored by thin-layer chromatography. Once the reaction iscomplete, the mixture is filtered and the filtrate is evaporated undervacuum to give a vitrified oil, which is taken up in a mixture of etherand methanol to give 1.16 g of a white solid recovered by filtration andidentified as N,N″-(2,3-dihydroxypropyl)sulfamide.

Melting point: 80-81° C. (ether/methanol).

Elemental analysis:

% C H N O S Calculated 29.5 6.6 11.5 39.5 13.1 Experimental 29.6 6.611.3 39.2 13.1

EXAMPLE 2 Synthesis of 2-[(aminosulfonyl)amino]ethyl sulfamate (Compound17)

To 4.35 ml of chlorosulfonyl isocyanate in 25 ml of dichloromethane isadded dropwise, at 0° C., a solution of 4.78 ml of tert-butanol in 25 mlof dichloromethane. The reaction medium is stirred for 10 minutes at 20°C. and is then added dropwise to a solution of 3.01 ml of ethanolamineand 7.66 ml of triethylamine in 60 ml of dichloromethane at 0° C. Afterraising the temperature to 20° C. and stirring overnight, the reactionmixture is diluted with dichloromethane and washed 3 times with dilutehydrochloric acid. The organic phase is then washed 3 times with waterand is then dried over sodium sulfate and concentrated under reducedpressure to give 5 g of a white solid identified as2-({[(tert-butoxycarbonyl)amino]sulfonyl}amino)ethyltert-butoxycarbonylsulfamate, which may be used in unmodified form.

To 1.5 g of 2-({[(tert-butoxycarbonypamino]sulfonyl}amino)ethyltert-butoxycarbonylsulfamate in 30 ml of dichloromethane are added 30 mlof a 1/1 trifluoroacetic acid/dichloromethane mixture. After stirringfor 4 hours at 20° C., the reaction mixture is concentrated underreduced pressure and taken up 3 times in ether and reevaporated. Thewhite solid is taken up in dichloromethane and filtered under vacuum togive 700 mg of the desired product: 2-[(aminosulfonyl)amino]ethylsulfamate.

Melting point: 78-82° C. (ether/dichloromethane).

Elemental analysis:

% C H N O S Calculated 11 4.1 19.2 36.5 29.3 Experimental 11.7 4.2 18.635.1 29.4

EXAMPLE 3 Synthesis of (±)-1,2,7-thiadiazepane-4,5-diol 1,1-dioxide(Compound 19)

To 1.5 g of (±)-4,5-di(aminomethyl)-2,2-dimethyl dioxolane in 30 ml ofdimethylformamide are added 1.08 g of sulfamide and 301 μl ofdiazabicycloundecene. The reaction mixture is then heated at 140° C. forseveral hours until conversion is complete. After evaporating off thedimethylformamide, the crude reaction product is chromatographed on acolumn of silica to give 1.5 g of an orange solid. This solid is thentaken up in pentane to give 1.2 g of a solid identified as2,2-dimethylhexahydro[1,3]dioxolo[4,5-d][1,2,7]thiadiazepine6,6-dioxide.

To 500 mg of2,2-dimethylhexahydro[1,3]dioxolo[4,5-d][1,2,7]thiadiazepine 6,6-dioxidesuspended in 10 ml of water are added Dowex® 50WX8 acidic resin, sold byAldrich, and 2 ml of tetrahydrofuran. The reaction medium is stirred atroom temperature overnight to give, after filtering off the resin andevaporating off the water, a vitrified paste that is taken up in etherand methanol to give 380 mg of a pale yellow solid identified as(±)-1,2,7-thiadiazepane-4,5-diol 1,1-dioxide.

Melting point: 188-192° C. (ether/methanol)

Elemental analysis:

% C H N O S Calculated 26.4 5.5 15.4 35.1 17.6 Experimental 26.5 5.515.3 34.7 17.6

EXAMPLE 4 Synthesis of N-(2-hydroxyethyl)sulfamide (Compound 2)

To 2.17 ml of chlorosulfonyl isocyanate in 10 ml of dichloromethane isadded dropwise, at 0° C., a solution of 2.39 ml of tert-butanol in 10 mlof dichloromethane. The reaction medium is stirred for 30 minutes at 0°C., followed by dropwise addition of 10.4 ml of triethylamine. Afterstirring for 30 minutes, 1.58 ml of ethanolamine are added dropwise at0° C.

After warming to 20° C. and stirring overnight, the reaction mixture isconcentrated under vacuum and the crude product is then diluted withdichloromethane and water and also with 0.1N hydrochloric acid. Theaqueous phase is then acidified with 1N hydrochloric acid and extractedthree times with ethyl acetate. The organic phases are washed withsaturated sodium chloride solution and then dried over sodium sulfate.After evaporation, 2.5 g of a white solid are obtained, dried undervacuum and identified as N(tert-butoxycarbonyl)-N″-(2-hydroxyethyl)sulfamide.

1 g of N-(tert-butoxycarbonyl)-N″-(2-hydroxyethyl)sulfamide is suspendedin 10 ml of 1N hydrochloric acid with stirring at room temperature.After reacting overnight, the reaction monitored by thin-layerchromatography is complete. The reaction medium is concentrated undervacuum and then co-evaporated several times with ethanol to give 520 mgof a colourless oil identified as N-(2-hydroxyethyl)sulfamide.

Elemental analysis:

% C H O S Calculated 17.1 5.8 34.2 22.9 Experimental 17.06 5.4 35 23

EXAMPLE 5 Synthesis of N-(2,3-dihydroxypropyl)sulfamide (Compound 4)

Procedure identical to that for N-(2-hydroxyethyl)sulfamide of Example4, with 2,3-dihydroxypropylamine as amine, which gives the compound:N-(tert-butoxy-carbonyl)-N″-(2,3-dihydroxypropyl)sulfamide, which isthen deprotected with hydrochloric acid as for the compound of Example5, to give a colourless oil identified asN-(2,3-dihydroxypropyl)sulfamide.

Elemental analysis: Presence of 0.75H₂O per mole

% C H N O S Calculated 21.1 5.9 16.4 37.6 18.8 Calculated with 19.6 6.215.2 41.4 17.4 0.75 H₂O Experimental 19.9 5.8 14.8 38.3 17.3

EXAMPLE 6 Synthesis of N-[bis(trimethylsilyl)methyl]sulfamide (Compound9)

The procedure is identical to that for the compound of Example 4, withbis(trimethylsilyl)methylamine as amine, to give the protected compound:N-(tert-butoxycarbonyl)-N″-(bis(trimethylsilyl)methyl)sulfamide.

However, the deprotection process is performed differently. To asolution of 30 ml of dichloromethane and 30 ml trifluoroacetic acid areadded, at 0° C., 2 grams ofN-(tert-butoxycarbonyl)-N″-(bis(trimethylsilyl)methyl)sulfamide. Thereaction progress is monitored by thin-layer chromatography. Afterreacting overnight, the reaction medium is concentrated under vacuum,taken up and co-evaporated with diethyl ether and dichloromethane. Thepaste obtained is then purified on a column of silica to give 500 mg ofa white solid identified as N-[bis(trimethylsilyl)methyl]sulfamide.

Melting point: 76-77.5° C. (dichloromethane).

Elemental analysis:

% C H N S Calculated 33 8.7 11 12.6 Experimental 33 8.5 11.1 11.9

EXAMPLE 7 Synthesis ofN-[bis(trimethylsilyl)methyl]-N″-(2-hydroxyethyl)sulfamide (Compound 15)

To 2.18 ml of chlorosulfonyl isocyanate in 10 ml of dichloromethane isadded dropwise, at 0° C., a solution of 1.77 ml of bromoethanol in 10 mlof dichloromethane. The reaction medium is stirred for 10 minutes at 0°C. and then added dropwise to a solution of 4.38 grams ofbis(trimethylsilyl)methylamine and 3.51 ml of triethylamine in 40 ml ofdichloromethane at 0° C. After warming to 20° C. and stirring for 4hours, the reaction mixture is cooled to 0° C. and 10.5 ml oftriethylamine are then added dropwise. The reaction mixture is thenstirred overnight at room temperature. It is then diluted withdichloromethane and washed 3 times with dilute hydrochloric acid. Theorganic phase is then washed once with saturated aqueous NaCl solutionand then dried over sodium sulfate and concentrated under reducedpressure to give a white solid, 2-oxooxazolidine-3-sulfonic acid[bis(trimethylsilanyl)methyl]amide (65% yield).

To 1 g of 2-oxooxazolidine-3-sulfonic acid[bis(trimethylsilanyl)methyl]amide suspended in 4 ml of ethanol areadded 10 ml of 2N sodium hydroxide at room temperature. The reactionmixture is thus stirred for 2 days at room temperature to convert theproduct. The reaction medium is extracted 3 times with ethyl acetate.The organic phase is dried over sodium sulfate and concentrated undervacuum to give a solid, which is then washed with a pentane/ethermixture.

Melting point: 104-106° C. (pentane/ether).

Elemental analysis:

% C H N S Calculated 36.2 8.8 9.4 10.7 Experimental 35.7 8.66 9.3 10.79

EXAMPLE 8 Synthesis of N,N′-bis(2-hydroxyethyl)sulfamide (Compound 10)

17 g of sulfonylbisoxazolidinone are added to 2N sodium hydroxidesolution (170 ml of water for 13.6 g of NaOH) and placed under stirring.After a strong evolution of CO₂, the reaction medium is stirred for 3days at room temperature. The reaction medium is then passed throughDowex® 50WX8-200 resin (sold by Aldrich). The resin is filtered througha sinter funnel and the filtrate is concentrated under vacuum. Theresidue is purified by flash chromatography on silica (eluent: 8/2EtOAc/MeOH). The volatile materials are evaporated off under vacuum togive a colourless oil (87% yield).

Elemental analysis:

% C H N O S Calculated pure 26 6.5 15.2 34.7 17.4 product Calculated24.9 6.7 14.5 37.3 16.6 product with 0.5 mol of water Experimental 256.6 14.5 36.7 17

EXAMPLE 9 Evaluation of the Moisturizing Potential

Two tests were performed to evaluate the moisturizing potential of thecompounds of the invention formulated in an aqueous 3% solution (exceptfor compounds 9 and 15, which were evaluated in a solution of isopropylN-lauroyl sarcosinate).

Dermometer, mechanical measurement of the plasticizing effect (describedby J. de Rigal, J-L. Leveque, International Journal of Cosmetic Science,1982, 247-260),

Transepidermal Water Loss (TWL), evaluation of the changes in barrierfunction of the stratum corneum.

Dermometer

The tests carried out were performed under standard conditions onstratum corneum in a room with regulated temperature and humidity (T=30°C. and RH=75%). The modulus of elasticity measurements are performed oneach control specimen and then 2 hours and 20 hours after application ofthe treatment. The relative variation in the modulus allows assessmentof the plasticizing effect of the active agent on the stratum corneum.

Transepidermal Water Loss (TWL)

Transepidermal water loss is a physiological phenomenon of diffusion ofwater vapour across the horny layer. It results from the presence of ahigh pressure gradient of water vapour between the internal and externalmedia of the body. The TWL depends on the integrity of the barrierfunction of the stratum corneum. The machine evaluating the TWL(Evaporimeter EP1, Servomed) measures the flow of water that diffusespassively across the stratum corneum (g/m²/h).

The isolated stratum is placed (inner face) on a water tank andequilibrated in a room regulated at 40% relative humidity (T=30° C.).Before the measurement, the stratum corneum is defatted via a two-hourtreatment in a mixture of chloroform and methanol (2 v/lv). For eachmeasurement, the TWL is measured on the stratum corneum before treatmentand then 2 and 20 hours after application of the treatment. The relativevariation in the TWL allows assessment of the change in the barrierproperty of the stratum corneum. The measurements are analysed in pairs.For each product, 8 measurements are taken on 2 batches of stratumcorneum.

The technique allows measurement of the flow of water that diffusespassively across a membrane of stratum corneum. This measurement takesinto account the integrity of the barrier function of the stratumcorneum. In the protocol used, the stratum corneum is defatted via atwo-hour treatment in a mixture of chloroform and methanol (2 v/lv). Themeasurements are taken on the control stratum corneum and then 2 hoursand 20 hours after application of the product. The relative variation inthe TWL allows assessment of the change in the barrier property of thestratum corneum.

TABLE 2 Dermometer measurements: Relative variation in the modulus ofelasticity of stratum corneum at 30° C. and 75% relative humidity, 2hours and 20 hours after application of the active agent Mean ± standarddeviation Product 2 h 20 h

−57 ± 7%  −68 ± 8% 

−46 ± 13% −63 ± 14%

−41 ± 17% −54 ± 15%

−25 ± 19% −34 ± 19%

−40 ± 16% −49 ± 14%

−27 ± 15% −29 ± 13%

−28 ± 15% −31 ± 24%

−34 ± 14% −44 ± 14%

−20 ± 6%  -24 ± 10% Control products Untreated stratum corneum −4 ± 5%−10 ± 5%  Pure water  −5 ± 10%  −2 ± 12% Isopropyl N-lauroylsarcosinate¹−18 ± 18% −20 ± 22% 3% urea in water −72 ± 9%  −83 ± 7%  3% glycerol inwater −41 ± 12% −51 ± 15% ¹sold under the name Eldew SL205 ® by thecompany Ajinomoto.

The mean and the standard deviation were calculated on 6 to 10 samples.

TABLE 3 Relative variation of the TWL measurements 2 hours and 20 hoursafter application of the active agent (Mean ± standard deviation)Product 2 h 20 h

  42.4 ± 22.6%   37.1 ± 21.1%

    38 ± 18%       37 ± 17%  

    13 ± 11%       1 ± 10%  

  −3 ± 5%    −4.5 ± 5%  

  31.5 ± 22.1%   21.1 ± 6.0% 

   4.6 ± 9.4%     1.0 ± 6.0% 

    1 ± 8%       1 ± 5%  

    18 ± 15%    −0.5 ± 10%   Control products Pure water    3.5 ± 10%  −1.7 ± 5.1% Isopropyl N-lauroylsarcosinate ¹    0.2 ± 7%     −7 ± 4%  3% urea in water   64.3 ± 26.9%   48.3 ± 24.5% 3% glycerol in water  41.2 ± 19.0%    3.1 ± 20.3% ¹ sold under the name Eldew SL205 ® by thecompany Ajinomoto.

The mean and the standard deviation were calculated on 8 samplesdistributed over 2 batches of stratum corneum.

It emerges from these tests that the compounds according to theinvention have different “moisturizing” profiles by plasticizing thestratum corneum and by modifying or not modifying the barrier function.

EXAMPLE 10 Cosmetic Formulations Example 10.1 Skincare Cream

PHASE A Glyceryl stearate (and) PEG-100 stearate 2.00 g Dimyristyltartrate (and) cetearyl alcohol (and) 1.50 g C12-15 pareth-7 (and)PPG-25 laureth-25 Cyclohexasiloxane 5.00 g Stearyl alcohol 1.00 g PHASEB Water QS 100 g Pentasodium ethylene diamine tetramethylene 0.05 gphosphate Ammonium polyacryldimethyltauramide: 0.40 g Xanthan gum 0.20 gPHASE C Compound 4 3.00 to 5.00 g Glycerol 1.50 g Adenosine 0.10 g Water3.00 gProcedure

Phase B is heated to about 75° C. and the ammoniumpolyacryldimethyltauramide is incorporated therein; the mixture isstirred until a homogeneous gel is obtained.

Phase A is heated to about 75° C.

The emulsion is prepared by incorporating Phase A into Phase B.

At 40-45° C., Phase C is incorporated, and stirring is continued untilthe mixture has completely cooled.

Skincare creams were also prepared according to this formulation withcompounds 1, 3, 6, 7, 9, 13, 15, 16 and 19.

Example 10.2 Skincare Cream

Compound 2 3.0 to 6.0% Glyceryl monostearate 0.8% Cetyl alcohol 2.0%Stearyl alcohol 5.0% Polyoxyethylene stearate (20 OE) 3.0% Crosslinkedacrylic acid (Carbopol 941) 0.3% Caprylic/capric triglycerides 12.0%Preserving agents qs Water qs 100.0%

Skincare creams were also prepared according to this formulation withcompounds 5, 8, 10, 11, 12, 14, 17 and 18.

The illustrated cosmetic formulations applied to the skin show a goodskin moisturizing effect.

Although the present invention herein has been described with referenceto particular embodiments, it is to be understood that these embodimentsare merely illustrative of the principles and applications of thepresent invention. It is therefore to be understood that numerousmodifications may be made to the illustrative embodiments and that otherarrangements may be devised without departing from the spirit and scopeof the present invention as defined by the appended claims.

1. A cosmetic method for at least one of non-therapeutic skincare andfor making up the skin, comprising applying to the skin at least onecosmetic composition comprising a compound of formula (IV), a saltthereof, or a mixture thereof,

in which: X and X′ represent, independently of each other, a hydrogenatom, a (C₁-C₆)alkyl group or a group such that —OX and/or —OX′represent(s) a phosphate or sulfate group and Y and Y′ represent,independently of each other, a hydrogen atom, a group —CH₂Z, in which Zrepresents an amine group or a group —NR⁶R⁷ or —OR⁵, with the provisothat when X and X′ simultaneously represent a group —CH₃, then Y and Y′are not simultaneously a hydrogen atom, or alternatively at least one ofthe groups

forms, independently of each other, a dimethyldioxolane group, oralternatively: X and X′ are hydrogen atoms and Y and Y′ together form acovalent bond, R¹ and R³ represent, independently of each other ahydrogen atom, a (C₁-C₁₀)alkyl group, or alternatively (R¹ and R³) form,with the group —N—(SO₂)—N— that bears them, a 5- to 9-memberedheterocycle, R⁵, R⁶ and R⁷ represent, independently of each other, ahydrogen atom, a (C₁-C₆)alkyl group, and R⁵ can also represent a groupsuch that —OR⁵ represents a phosphate or sulfate group.
 2. The methodaccording to claim 1, wherein the method is for moisturizing the skin.3. The method according to claim 1, the compound of formula (IV) isN,N″-bis(hydroxyethyl)sulfamide of formula:


4. A cosmetic composition comprising, in a physiologically acceptablemedium, a compound of formula (IV), a salt thereof, or a mixturethereof,

in which: X and X′ represent, independently of each other, a hydrogenatom, a (C₁-C₆)alkyl group or a group such that —OX and/or —OX′represent(s) a phosphate or sulfate group and Y and Y′ represent,independently of each other, a hydrogen atom, a group —CH₂Z, in which Zrepresents an amine group or a group —NR⁶R⁷ or —OR⁵, with the provisothat when X and X′ simultaneously represent a group —CH₃, then Y and Y′are not simultaneously a hydrogen atom, or alternatively at least one ofthe groups

forms, independently of each other, a dimethyldioxolane group, oralternatively: X and X′ are hydrogen atoms and Y and Y′ together form acovalent bond, R¹ and R³ represent, independently of each other ahydrogen atom, a (C₁-C₁₀)alkyl group, or alternatively (R¹ and R³) form,with the group —N—(SO₂)—N— that bears them, a 5- to 9-memberedheterocycle, R⁵, R⁶ and R⁷ represent, independently of each other, ahydrogen atom, a (C₁-C₆)alkyl group, and R⁵ can also represent a groupsuch that —OR⁵ represents a phosphate or sulfate group.
 5. The cosmeticcomposition according to claim 4, further comprising another skinmoisturizer.
 6. The cosmetic composition according to claim 4, whereinthe composition is intended for non-therapeutic skincare.
 7. Thecosmetic composition according to claim 4, comprising at least onemember selected from the group consisting of oils, fatty substances,emulsifiers, gelling agents, film-forming polymers, preserving agents,solvents, fragrances, fillers, UV-screening agents, bactericides, odourabsorbers, dyestuffs, plant extracts and salts.
 8. A dermatologicalmethod for moisturizing skin comprising applying to the skin thecosmetic composition according to claim 4.